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#$Date: 2016-03-23 21:04:08 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179438 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/35/4333568.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4333568
loop_
_publ_author_name
'Mohammad Reza Halvagar'
'Benjamin Neisen'
'William B. Tolman'
_publ_contact_author_email       wtolman@umn.edu
_publ_contact_author_name        'William B. Tolman'
_publ_section_title
;
 Copper-, Palladium-, and Platinum-Containing Complexes of an Asymmetric
 Dinucleating Ligand
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              793
_journal_page_last               799
_journal_paper_doi               10.1021/ic301914u
_journal_volume                  52
_journal_year                    2013
_chemical_formula_moiety         'C28 H34 Cl2 N6 O2 Pd and O'
_chemical_formula_sum            'C28 H34 Cl2 N6 O3 Pd'
_chemical_formula_weight         679.91
_chemical_name_common            LH2PdCl2
_chemical_name_systematic        8
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      11
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.88
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.139
_cell_length_b                   13.516
_cell_length_c                   11.774
_cell_measurement_reflns_used    3845
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      20.01
_cell_measurement_theta_min      1.76
_cell_volume                     1432.787
_computing_cell_refinement       'SMART, Bruker'
_computing_data_collection       'SMART, Bruker'
_computing_data_reduction        'SMART, Bruker'
_computing_publication_material  'SMART, Bruker'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker SMART Platform, CCD'
_diffrn_measurement_method       'area detector, omega scans per phi'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1063
_diffrn_reflns_av_sigmaI/netI    0.0952
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3845
_diffrn_reflns_theta_full        20.01
_diffrn_reflns_theta_max         20.01
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.876
_exptl_absorpt_correction_T_max  0.9742
_exptl_absorpt_correction_T_min  0.9175
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing, 1995'
_exptl_crystal_colour            yellow-brown
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_recrystallization_method
'Et2O slowly diffused into solution of 10 in MeCN'
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.689
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1366
_refine_ls_number_restraints     180
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0576
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0626P)²+0.0854P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1392
_reflns_number_gt                924
_reflns_number_total             1366
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic301914u_si_002_4.cif
_cod_data_source_block           8
_cod_original_cell_volume        1432.8
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               4333568
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.0962(4) 0.2500 0.0109(3) 0.095(6) Uani 1 2 d SU
H1 H 0.1523 0.2500 0.0867 0.114 Uiso 1 2 calc SR
C2 C 0.0527(4) 0.3364 -0.0478(3) 0.076(4) Uani 1 1 d RU
H2 H 0.0810 0.3972 -0.0139 0.091 Uiso 1 1 d R
C3 C -0.0311(4) 0.3330 -0.1547(3) 0.056(3) Uani 1 1 d RU
C4 C -0.0721(4) 0.4250 -0.2259(3) 0.056(3) Uani 1 1 d RU
C5 C -0.1980(4) 0.4727 -0.4212(3) 0.053(3) Uani 1 1 d RDU
C6 C -0.1194(4) 0.5591 -0.4326(3) 0.099(4) Uani 1 1 d RDU
H6 H -0.0429 0.5784 -0.3742 0.119 Uiso 1 1 d R
C7 C -0.1551(4) 0.6168 -0.5312(3) 0.115(5) Uani 1 1 d RDU
H7 H -0.1025 0.6746 -0.5388 0.138 Uiso 1 1 d R
C8 C -0.2695(4) 0.5879 -0.6185(3) 0.092(4) Uani 1 1 d RDU
H8 H -0.2934 0.6265 -0.6845 0.110 Uiso 1 1 d R
C9 C -0.3481(4) 0.5015 -0.6072(3) 0.059(3) Uani 1 1 d RDU
C10 C -0.3124(4) 0.4439 -0.5085(3) 0.045(2) Uani 1 1 d RDU
H10 H -0.3650 0.3860 -0.5009 0.054 Uiso 1 1 d R
C11 C -0.4807(12) 0.4753(9) -0.6973(8) 0.075(3) Uani 1 1 d U
H11A H -0.5591 0.4481 -0.6578 0.090 Uiso 1 1 calc R
H11B H -0.5199 0.5370 -0.7367 0.090 Uiso 1 1 calc R
C13 C -0.5872(11) 0.4102(11) -0.8787(8) 0.104(5) Uani 1 1 d U
H13A H -0.6746 0.3869 -0.8485 0.156 Uiso 1 1 calc R
H13B H -0.5725 0.3690 -0.9442 0.156 Uiso 1 1 calc R
H13C H -0.6025 0.4791 -0.9040 0.156 Uiso 1 1 calc R
C14 C -0.1286(12) 0.2500 -0.7440(10) 0.048(4) Uani 1 2 d SU
H14A H -0.0482 0.2831 -0.7745 0.072 Uiso 0.50 1 calc PR
H14B H -0.0996 0.1817 -0.7234 0.072 Uiso 0.50 1 calc PR
H14C H -0.1481 0.2852 -0.6754 0.072 Uiso 0.50 1 calc PR
C15 C -0.2727(10) 0.3416(8) -0.9047(7) 0.053(3) Uani 1 1 d U
H15A H -0.3468 0.3323 -0.9758 0.064 Uiso 1 1 calc R
H15B H -0.1753 0.3561 -0.9271 0.064 Uiso 1 1 calc R
C16 C -0.31932(10) 0.4268(3) -0.83339(8) 0.059(3) Uani 1 1 d U
H16A H -0.2370 0.4420 -0.7695 0.071 Uiso 1 1 calc R
H16B H -0.3380 0.4864 -0.8826 0.071 Uiso 1 1 calc R
N1 N -0.07569(10) 0.2500(3) -0.21229(8) 0.046(3) Uani 1 2 d SRU
N2 N -0.16367(10) 0.4090(3) -0.32495(8) 0.047(2) Uani 1 1 d RDU
H2N2 H -0.2284 0.3498 -0.3552 0.056 Uiso 1 1 d RD
N3 N -0.45258(10) 0.4037(3) -0.78575(8) 0.062(2) Uani 1 1 d RU
N4 N -0.26261(10) 0.2500(3) -0.83150(8) 0.043(3) Uani 1 2 d SRU
O1 O -0.01899(10) 0.5073(3) -0.18854(8) 0.099(3) Uani 1 1 d RU
O2 O -0.40974(10) 0.2500(3) -0.35920(8) 0.045(2) Uani 1 2 d SR
Cl1 Cl -0.63568(10) 0.2500(3) -0.65137(8) 0.0872(15) Uani 1 2 d SRU
Cl2 Cl -0.55034(10) 0.2500(3) -0.13852(8) 0.1015(19) Uani 1 2 d SR
Pd1 Pd -0.44467(10) 0.2500(3) -0.75387(8) 0.0555(6) Uani 1 2 d SRU
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 C2 115.6 4_565 .
C2 C1 H1 122.2 4_565 .
C2 C1 H1 122.2 . .
C3 C2 C1 120.3 . .
C3 C2 H2 119.9 . .
C1 C2 H2 119.9 . .
N1 C3 C2 124.93(18) . .
N1 C3 C4 112.55(18) . .
C2 C3 C4 122.3 . .
O1 C4 N2 126.5(3) . .
O1 C4 C3 119.17(19) . .
N2 C4 C3 114.35(18) . .
C6 C5 C10 120.0 . .
C6 C5 N2 122.75(16) . .
C10 C5 N2 117.21(16) . .
C7 C6 C5 120.0 . .
C7 C6 H6 120.0 . .
C5 C6 H6 120.0 . .
C6 C7 C8 120.0 . .
C6 C7 H7 120.0 . .
C8 C7 H7 120.0 . .
C9 C8 C7 120.0 . .
C9 C8 H8 120.0 . .
C7 C8 H8 120.0 . .
C10 C9 C8 120.0 . .
C10 C9 C11 120.1(4) . .
C8 C9 C11 119.7(4) . .
C9 C10 C5 120.0 . .
C9 C10 H10 120.0 . .
C5 C10 H10 120.0 . .
N3 C11 C9 115.7(6) . .
N3 C11 H11A 108.4 . .
C9 C11 H11A 108.4 . .
N3 C11 H11B 108.4 . .
C9 C11 H11B 108.4 . .
H11A C11 H11B 107.4 . .
N3 C13 H13A 109.5 . .
N3 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
N3 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
N4 C14 H14A 109.5 . .
N4 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
N4 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
N4 C15 C16 107.5(5) . .
N4 C15 H15A 110.2 . .
C16 C15 H15A 110.2 . .
N4 C15 H15B 110.2 . .
C16 C15 H15B 110.2 . .
H15A C15 H15B 108.5 . .
N3 C16 C15 112.3(4) . .
N3 C16 H16A 109.1 . .
C15 C16 H16A 109.1 . .
N3 C16 H16B 109.1 . .
C15 C16 H16B 109.1 . .
H16A C16 H16B 107.9 . .
C3 N1 C3 114.0(3) . 4_565
C4 N2 C5 128.5(3) . .
C4 N2 H2N2 132.2 . .
C5 N2 H2N2 99.3 . .
C16 N3 C11 112.9(5) . .
C16 N3 C13 109.9(4) . .
C11 N3 C13 104.8(6) . .
C16 N3 Pd1 105.9 . .
C11 N3 Pd1 121.7(4) . .
C13 N3 Pd1 100.7(6) . .
C14 N4 C15 111.5(5) . .
C14 N4 C15 111.5(5) . 4_565
C15 N4 C15 111.0(7) . 4_565
C14 N4 Pd1 109.6(5) . .
C15 N4 Pd1 106.5(3) . .
C15 N4 Pd1 106.5(3) 4_565 .
N4 Pd1 N3 85.7 . .
N4 Pd1 N3 85.7 . 4_565
N3 Pd1 N3 159.8 . 4_565
N4 Pd1 Cl1 175.0 . .
N3 Pd1 Cl1 95.0 . .
N3 Pd1 Cl1 95.0 4_565 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.3798 4_565
C1 C2 1.3798 .
C1 H1 0.9500 .
C2 C3 1.3573 .
C2 H2 0.9300 .
C3 N1 1.338(4) .
C3 C4 1.5104 .
C4 O1 1.263(4) .
C4 N2 1.331(4) .
C5 C6 1.3900 .
C5 C10 1.3900 .
C5 N2 1.415(4) .
C6 C7 1.3900 .
C6 H6 0.9300 .
C7 C8 1.3900 .
C7 H7 0.9300 .
C8 C9 1.3900 .
C8 H8 0.9300 .
C9 C10 1.3900 .
C9 C11 1.509(12) .
C10 H10 0.9300 .
C11 N3 1.477(11) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C13 N3 1.502(9) .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 N4 1.459(11) .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 N4 1.503(10) .
C15 C16 1.528(10) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 N3 1.4593 .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
N1 C3 1.338(4) 4_565
N2 H2N2 1.0220 .
N3 Pd1 2.1099 .
N4 C15 1.502(10) 4_565
N4 Pd1 2.0312 .
Cl1 Pd1 2.2861 .
Pd1 N3 2.109(8) 4_565
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C2 C1 C2 C3 1.9 4_565 .
C1 C2 C3 N1 -1.25(17) . .
C1 C2 C3 C4 -175.5 . .
N1 C3 C4 O1 -170.0(3) . .
C2 C3 C4 O1 4.83(17) . .
N1 C3 C4 N2 9.8 . .
C2 C3 C4 N2 -175.32(15) . .
C10 C5 C6 C7 0.0 . .
N2 C5 C6 C7 177.66(17) . .
C5 C6 C7 C8 0.0 . .
C6 C7 C8 C9 0.0 . .
C7 C8 C9 C10 0.0 . .
C7 C8 C9 C11 174.6(4) . .
C8 C9 C10 C5 0.0 . .
C11 C9 C10 C5 -174.6(4) . .
C6 C5 C10 C9 0.0 . .
N2 C5 C10 C9 -177.79(16) . .
C10 C9 C11 N3 -87.0(7) . .
C8 C9 C11 N3 98.3(7) . .
N4 C15 C16 N3 -52.4(6) . .
C2 C3 N1 C3 0.4(3) . 4_565
C4 C3 N1 C3 175.15(15) . 4_565
O1 C4 N2 C5 14.8(6) . .
C3 C4 N2 C5 -165.0(2) . .
C6 C5 N2 C4 10.6(4) . .
C10 C5 N2 C4 -171.7(2) . .
C15 C16 N3 C11 167.7(6) . .
C15 C16 N3 C13 -75.7(7) . .
C15 C16 N3 Pd1 32.3(4) . .
C9 C11 N3 C16 -46.6(8) . .
C9 C11 N3 C13 -166.2(8) . .
C9 C11 N3 Pd1 80.9(8) . .
C16 C15 N4 C14 -75.7(7) . .
C16 C15 N4 C15 159.31(18) . 4_565
C16 C15 N4 Pd1 43.8(6) . .
C14 N4 Pd1 N3 99.15(18) . .
C15 N4 Pd1 N3 -21.6(4) . .
C15 N4 Pd1 N3 -140.1(4) 4_565 .
C14 N4 Pd1 N3 -99.2(2) . 4_565
C15 N4 Pd1 N3 140.1(4) . 4_565
C15 N4 Pd1 N3 21.6(4) 4_565 4_565
C14 N4 Pd1 Cl1 -0.01(18) . .
C15 N4 Pd1 Cl1 -120.8(4) . .
C15 N4 Pd1 Cl1 120.8(4) 4_565 .
C16 N3 Pd1 N4 -5.6 . .
C11 N3 Pd1 N4 -136.1(5) . .
C13 N3 Pd1 N4 108.9(4) . .
C16 N3 Pd1 N3 -70.8 . 4_565
C11 N3 Pd1 N3 158.7(5) . 4_565
C13 N3 Pd1 N3 43.7(4) . 4_565
C16 N3 Pd1 Cl1 169.5 . .
C11 N3 Pd1 Cl1 38.9(5) . .
C13 N3 Pd1 Cl1 -76.0(4) . .
